ON THE ASYMMETRIC INDUCTION INVOLVING LITHIUM ENOLATES OF L-MENTHYLPROPIONATE

Authors
RIBEIRO LP ANTUNES OAC BERGTER L COSTA PRR
Citation
Lp. Ribeiro et al., ON THE ASYMMETRIC INDUCTION INVOLVING LITHIUM ENOLATES OF L-MENTHYLPROPIONATE, Tetrahedron : asymmetry, 5(10), 1994, pp. 1873-1874
Citations number
13
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
5
Issue
10
Year of publication
1994
Pages
1873 - 1874
Database
ISI
SICI code
0957-4166(1994)5:10<1873:OTAIIL>2.0.ZU;2-X
Abstract
The stereoselectivities of the reaction between 1-methylpropionate 1 w ith LDA under standard kinetic conditions depend on the solvent. The Z -enolate 2a predominates in LDA/THF (Z/E=7.5/2.5) while the E-enolate 3a is the main product in LDA/THF/hexane (E/Z=8/2). The mixture of the se enolates (E/Z=8/2) was allowed to react with allylbromide, benzalde hyde and MoOPH respectivelly. The higher pi-facial diastereoselection was obtained from MoOPH (d.e.=60%).